Hi everyone!

I am trying to find ideas for creating a twist on pineapple upside down cake but I haven't had much luck and I find it rather baffling. It's for my boyfriend's birthday because it's his favorite cake, but the traditional method doesn't allow for decorating or really any creativity.

My idea won't be "upside down" at all, but here's what I'm thinking. A yellow cake made with pineapple juice and some crushed pineapple (I've done this part before), filled with caramelized crushed pineapple (with butter/brown sugar) and a light layer of vanilla buttercream, and also frosted with vanilla buttercream. I was wondering if I should do a pineapple buttercream instead, or switch to a cream cheese frosting.

Any thoughts or suggestions? I want a tiered layer cake with all of the pineapple upside down qualities but with the ability to frost and decorate. I don't like the idea of simply stacking 2 traditional pineapple upside down cakes and throwing frosting on it. I also don't want to spend time baking and creating a disaster, so input is greatly appreciated! :)

the only thing i'm coming up with is rum flavored splash  or a real rum splash for variety -- a splash of course is simple syrup and flavor or liqueur  -- simple syrup is equal parts sugar and water boiled till clear, cool , add flavor -- then squirt or brush onto baked cake layers

i like all your ideas -- i did a carmelized banana filling once and it seemed to loose the crispness -- was still great -- just saying -- pineapple is weird with liquids --

hey is there such a thing as a pineapple curd?

Sorta like a pea picking cake? I think Pea Picking cake is a southern name, but is uses canned mandarin oranges in the cake so similar idea. To me Pineapple upside down cake is pineapple, maraschino cherries and caramelized brown sugar. So don't forget the cherries! They happen to be my hubby's favorite part, ha ha.

I've done a pineapple compote filling before that was brown sugar and diced pineapple that was cooked down until thick and sticky (I think there might have been a little bit of corn starch to help thicken it).  It would be easy to add cherries to that.

A cream cheese frosting sounds good, or a thick whipped cream would be delicious.

brown sugar swiss meringue

wonder if you can make a browned butter swiss meringue